I just wanted to say my two bits: that last convo with him and his brother did not seem very kind to me. Baiting for other people to confess to feelings they don't want to confess to (maybe not even to themselves), even correcting for all the exhibitionism that YT and vlogging or podcasting culture, is not kind when you are just going to brush it off.
Ali, from whatever little I got a whiff from the three months of subscribing and watching him (I don't anymore as his content-probably driven to a YT audience-became saturated with product placements and recycled soundbytes), struck me as someone very cagey and inarticulate with anything in the domain of emotions (not least that hover around failure, messiness of adult life and randomness of life in general), despite all his achievements. He has often prided himself as being a cool rationalist and the cold certainty of so much of his YT advice-and-soundbyte dishing persona- which I suspect is a fairly small part of his life- benefits to a huge amount from this.
Anyways, the kind of conversation the matey brothers seemed to be aiming for required a friendlier platform if Ali is really grappling with these issues. You need to be sitting opposite someone who has the vocabulary, the fluency and the objectivity to really explore the kind of things Ali was talking about in that on-video podcast.
This is what counsellors and psychotherapists (and GPs with an interest in mental health) do. With ease. Everyday. Ali's brother, with all due respect, isn't one (not unsurprisingly didn't have anything of note for Ali to take from it) and looking at Ali's all-too-visible discomfort and inarticulacy and all the issues around hitting a roadblock with his book project, the online trolls etc I feel he could benefit from just having regular sessions with a counsellor to process these.
Since I have been redirected to the forum because of the comments he's read, I hope he is not discouraged enough to never come back and hopes to read this.
He needs time away from the spiral of these untrained self-help gurus and find something customised to him and his unmet emotional and psychological needs. May I suggest a personal deep dive with a counselor that is not being posted on YT for money?
I really don't mean to troll, I just got worried for his mental health.